


I Deserve to be Happy

by KassieProphet



Category: Supernatural
Genre: Angst, Castiel is a Little Shit, Dean is So Done, Eventual Happy Ending, Eventual Smut, Friends to Lovers, M/M, Mutual Pining, Slow Burn
Language: English
Status: In-Progress
Published: 2018-04-04
Updated: 2018-04-04
Packaged: 2019-04-18 05:25:12
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 14
Words: 9,120
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14206029
Author URL: https://archiveofourown.org/users/KassieProphet/pseuds/KassieProphet
Summary: Dean wants to be with Castiel, but is tired of waiting. Can Castiel work through his shit before he;s lost Dean for good?





	1. Chapter 1

Dean Winchester is an outrageous flirt. It is known. So no one really bats an eye at the cheesy one-liners Dean throws out at the new bartender at their local dive bar. Cas squints at him and Sam just rolls his eyes. No one comments that the new, _hot_ , bartender is a dude—Dean is an outrageous flirt.

When Dean needs to think, or he just wants to get the stink blown off him, he takes Baby out for a nice long drive. But sometimes he hits up the dive bar for a whiskey and chaser. The new guy—Tyson—apparently works part time, so it's not like Dean goes to the dive bar _just_ for him. Dean dishes it out to Bonnie too, although she dishes it right back in a way that reminds him way too much of Ellen for him to consider ever making a serious move on her.

 When Tyson works, he usually lets Dean stay until the bar is cleaned and locked up. It's maybe 2 months since Dean has been keeping Tyson company for close up when Tyson surprises him by making the first move.

Dean is pleasantly buzzed—not enough enough that he has to call a cab, but enough that he's Cas-level close to Tyson—laughing at some anecdote of Tyson's that he's telling while locking the front door of the bar.

"...and then she just... _drops it_ ," laughs Tyson.

"What? NO. She _didn't_ ," laughs Dean in turn. He claps Tyson on the shoulder, but his hand lingers there.

Tyson leans into it, and before Dean has a chance to even consider the movement, Tyson is shifting forward and pressing his lips against Dean's.

The kiss is not unwelcome, but it does take Dean a bit off guard, so instead of enthusiastically reciprocating, he stands there like a cold fish.

Tyson backs off the second he realizes he is performing a one-man show.

"Uhhh..." says Dean intelligently.

Tyson's face crumples, then his eyes go wide and he holds his hands up, palm open in front of him.

"Oh shit! Sorry, man! Look, I guess I misread what was happening here, but..."

He takes a step back and Dean realizes Tyson thinks he's about to get the crap beat out of him.

Dean gropes for one of Tyson's hands, but when Tyson flinches, Dean takes a step back. He rubs the back of his neck self-consciously.

"Oh hey, wait. Um, no. You didn't...I just..." Dean blows out a puff of air, centering himself. "You didn't. Read this wrong, I mean."

Tyson visibly unclenches.

"I just, um. Wasn't actually expecting it to go anywhere."

The relaxed line of Tyson's body turns into a dejected slump.

"Oh."

Dean rubs his hand down his face. _Christ, when did he lose all his game?_

"Naw, man. I just meant: you work here; I drink here; and never the two do mix."

"Is that supposed to make me feel better?"

All his game. All of it.

"I meant I didn't think I stood a chance, dude. Not in my own backyard, anyway."

"Oh," says Tyson again, but this time it doesn't sound dejected. He steps toward Dean, taking one of his hands in his own. "You do. Stand a chance."

Tyson is rubbing circles with his thumb into the web of Dean's hand while giving him hopeful bedroom eyes. And all of a sudden Dean just feels...tired. Tyson's hot, yeah, and he's definitely got a card in Dean's spank bank catalogue...but Dean just doesn't think he has the energy to keep up the bravado of Lady Killer and Man Eater extraordinaire. Fuck it. He wants late nights, early mornings, and Netflix. Tyson seems to sense the shift in Dean's mood and drops his hand.

"I have to say, Dean: I'm getting whiplash with you here."

Dean knows Sam is always accusing him of being emotionally constipated and afraid of _feelings_ —and Chuck knows Dean's actually done nothing to abuse Sam of his notions—but Dean's not afraid to open the gates when it's safe. Know when it's not safe? When you're 2 days into a wendigo hunt and lives are on the line. When Chuck's freaking sister is eating the planet. But here? In this parking lot?

"I don't mean to kill the mood, Ty...but what are you expecting out of this?"

Tyson gives a humorless laugh and scrubs his face with both of his hands.

"We haven't even had a proper kiss and you're having The Relationship Talk with me, Dean? You know, what? Forget it."

He starts to walk away, but Dean grabs his wrist.

"Hey, man. It's not like that. I just. I'm pushing 40, dude. Maybe 5 years ago I still would have had it in me to rock your world and be gone before you woke up...but not anymore."

Tyson is looking down at where Dean's hand still encircles his wrist. Dean notices, and lets go. He runs it through his hair. Tyson crosses his arms.

"Your reputation has always proceeded you, Dean. 

Oh. _Oh_. Dean feels like he's been punched in the gut. He doesn't know why. It's not like he's ever been ashamed of his one night stands. Living out of the Impala and shitty motels rooms while trying to stop the Apocalypse of the week isn't really conducive to steady, romantic relationships. And none of the people he slept with were looking for that either. 

But this guy, who Dean had been starting to think of as at least a friend, has basically just called Dean a man whore. Dean Winchester: easy. And while he's never needed thanks for running the family business, he sure as fuck doesn't need to be shamed for finding little moments of relief between killing demons and banishing dick angels.

_See, Sam? This is what happens when you give in to the chick-flick moment._

Shit. He's going to have to find a new local haunt. _And_ try to explain to Sam  & Cas why without, you know...explaining why.

"I should go," Dean says. He turns and he can hear the gravel crunch under the twist of his boots. Fuck, he can't wait to get back to the Bunker. Maybe Cas will be around and they can finally watch _Stranger Things_.

He doesn't hear the Tyson's light footfalls on the stone—shit, he's getting soft—but he does feel Tyson's warm hand on his shoulder.

"Wait—Dean. I didn't...I didn't mean it like that." 

He comes around to face Dean. Dean stops, arms crossed. It's an invitation.

Tyson looks up him, brown eyes big, then bows his head, hands running up the back.

"Shit, Dean. I just meant I already know about that. And that I see past it."

Dean doesn't uncross his arms, but he eases his stance.

"Look, I can't tell you that I'm going to be your boyfriend. I thought...you seemed into me and I thought we'd go back to my place, have some hot sex, I'd make you eggs in the morning, and we'd...go from there."

A million thoughts hit Dean all at once: a desire to nuke the last 20 minutes from the record and do just that; a raw part of him saying to forget everything and never come back here; images of him making Tyson a frittata; the knowledge that no matter what Dean wants domestically, he's always going to hunt monsters and Tyson is a civilian.

It's Dean's turn to scrub down his face. 

"Yeah. Yeah, ok."

Tyson's face lights up.

"But, uh, I'm actually going to be out of town for a few days. Can we...can we pick this up when I get back?"

Disappointment flickers across Tyson's face briefly before he schools it into a neutral expression.

"I'm not blowing you off—really, man. You know that job I don't talk about?"

Tyson nods.

"I'm actually a...bounty hunter. Kinda a family business my mom & dad started. My brother and I took it over after they died. We got a lead on a new case. If this a problem..."

"No! It's actually kinda badass. I thought maybe military, but yeah. Bounty hunter. Makes more sense." 

They end up smiling shyly at each other and exchanging numbers.


	2. Chapter 2

Dean sits at the kitchen table with a bottle of whiskey. There actually is no case. Dean just has a lot to think about it. Thing is, despite everything he'd said to Tyson and himself, he's not sure he can do this. If he'd met Tyson on the road, Dean would have absolutely taken him for the one-night-only spin. Tyson's proximity to "home base" makes him appealing as a steady partner...but Lisa & Ben still feature in his mind—a wound long scared over but still prominent, ugly.

Then there's Cas. Dean is in love with Cas. It was always lust at first sight, but along the way it grew into something more. And, despite comments from the peanut gallery, Cas wants nothing to do with him. Not in that way, anyway.

Dean remembers after the disaster of the brothel offering himself up to Cas and Cas politely declining. The rejection stung a little, but hey: angel. The year with Lisa and Cas' civil war with heaven, however, made Dean wonder if Cas rejected him because he wanted more than just a quick roll in the hay. Dean wondered if he wanted more that a roll in the hay. He had tried to bring it up to Cas—before everything went to shit with the Purgatory souls—but Cas had made it clear that he had more important things to do than "have a liaison." Afterward, as Dean held the dripping trench coat, he wondered if Cas was just trying to soften the betrayal.

He'd tabled his feelings after that. They had Dick Roman to kill and then Purgatory to survive. But when Cas showed up in the motel room after Dean thought he was lost? Dean was so sure Cas would want him. Cas, however, had just sighed and tried to explain he just didn't feel that way about Dean. It had been a blow, but Dean was an adult and there were the trials to do and a prophet to keep safe. When they found out about Naomi's mind control, Dean had felt a little spark of hope. After they closed the Gates of Hell, he promised himself, he'd broach the subject with Cas.

And then everything went to shit. Again. Sam nearly dying. The angels falling. Cas becoming human and Dean failing him so irrevocably...Dean didn't just table his feelings for Cas—he'd crammed them in a box, stuffed that box deep down, then dug a moat around it. That he'd filled with alligators.

If that wasn't enough to destroy any hope Dean had ever have, then the Mark of Cain put the nail in the coffin. It's something that Cas and Dean don't talk about. All the vulgar, explicit, dirty texts Dean sent Cas when he was a demon. All the ways Dean told Cas that Crowley would be better lover than Cas could ever be. When Sam finally cured him, Dean had destroyed both cell phones. Cas didn't say anything when Dean gave him a brand new, fully-loaded smart phone.

And yet...and yet Cas never looked at him any differently. Cas' face still lit up when he saw Dean after either of them had been separated for any length of time. Cas, whom Dean had given a room in the Bunker. Cas who dropped by for his "pop-culture education" and who sent him texts at 3am filled with emojis that he'd learned from Claire. Cas who sat with his hands wrapped around a coffee at diners just so he could keep Dean company and who sat shotgun in Baby when Sam was in research mode or out on a solo case.

Dean had felt like he was going crazy. Cas had told him no. More than once. But except for the sex and intimacy, Dean was painfully aware that he was basically dating Cas. Everyone around him was painfully aware that he was dating Cas.

So, he'd tried again. Cas had cut him off before he'd even gotten a third of the way into it.

"No, Dean. I thought this was settled. I am not interested in engaging in a romantic relationship with you."

So Dean had let it go, even shrugging off Cas' clipped rejection. Dean just had continued "dating" Cas while seeking out sex elsewhere, thinking that this was as good as it got. These scraps of affection from Cas being good enough.

But, as he poured himself yet another shot of Jim, the aborted kiss with Tyson had made him realize just how miserable with the whole situation he was. He had Cas to hang with and people at bars to fuck...but he couldn't watch Netflix with his casual encounters, and he couldn't pull Cas into him as they sat side by side, eyes on his laptop. Memory foam for 1, please, and Dean was tired of it.

And maybe this thing with Tyson was a bad idea. Maybe it'd be a disaster. Chuck knows Dean is a moody SOB and doesn't plan on hanging up his gun any time soon. But Dean thinks he wants to try. Even if it only lasts a few weeks. Even if one day Dean comes by to find some demon trying to use Tyson and after Dean takes care of business they have to have The Talk.

He'll have to let Sam know, of course—they've both found out the hard way how dangerous it is to keep secrets—but he's also going to have to ask Cas. Dean knows it's a stupid thought—asking Cas' permission. Cas has made it very clear that there is no chance of a romantic relationship between the two of them...but Dean can't help but think he owes it to Cas. Tyson wouldn't be a one-night-stand. Tyson would potentially be Dean's...whatever. And right now Cas was Dean's...whatever. Especially considering the enthusiastic greeting Cas had given him after Dean had managed to avoid becoming a soul bomb for Amara. Cas deserves one last chance. 


	3. Chapter 3

As usual in Dean Winchester's life, nothing is easy.

Sam is out with Eileen, and Cas is still gone, so Dean forgoes making a big breakfast. Just some coffee and toast, and if he has one of Sam's tiny oranges, no one has to know. He's crunching down on part of the crust when he hears the bunker door open and footsteps.

"Hey, Sammy!" he calls around the toast. "I hope Eileen fed you because I ain't a restaurant!"

"Hello, Dean," says not-Sam. "I do not require breakfast, but I thought you might enjoy some pie."

Cas sets down two bags on the counter.

"Heya, Cas!" says Dean as he makes grabby hands for the pie.

Cas gives him a good approximation of one of Sam's bitchfaces with his own dom eyebrow thrown in for variation.

"You are more than capable of getting this yourself, Dean," Cas says, but he's already lifting the pie out of one of the bags and placing it within Dean's reach on the table.

"Fork?" Dean asks with Sam puppy-dog eyes #15.

Cas sighs, but he procures a plate, a knife, and a fork.

"Thanks, Cas," Dean says as he shoots Cas one of his megawatt smiles. It has the desired effect, and Cas rolls his eyes at Dean, but smiles in return as he shucks the other bag off of a six pack.

"Cas! Is it my birthday?" Dean exclaims, putting his hand over his heart.

"Dean. You know very well that your birthday isn't for another 4 months."

"What's with the beer and pie, Cas? You looking to get lucky?"

Cas gives him stink face as he places the beer in the fridge and says, "I have noticed you and Sam enjoy snacks and alcohol consumption when 'binge watching'. Consider this an offering."

Dean smiles, mouth full of pie. "Ah, I see. Just using me for my Netflix subscription, huh."

"No, Dean! I was merely—" Cas turns and sees the look on Dean's face, "oh, you were joking."

"Sit down, Cas," Dean says as he kicks out the chair across form him. "Whatcha been up to?"

Cas sighs and takes the offered seat. "Nothing of import, Dean. 'Angel shit' as you would say."

Dean puts his fork down, frowning. "They being dicks to you again, man? I got a banishing sigil with their names on it. Just say the word."

"Thank you, Dean," says Cas through a tired smile, "but that is unnecessary. As you know, not every angel desired to return to heaven. Hannah..." Cas trails off, "Hannah had thought it best to bring them back by force, a course action I am now ashamed I was a part of, but after Amara the angels 'let it go'."

"Hey, man. Don't get twisted up about that. That Hannah chick was your friend and you thought you were doing her a solid. We've all been there."

Cas' eyes are full of affection when he responds. "Yes, Dean. We usually are. But thank you for the sentiment, all the same."

"So how's this related?" Dean asks as he shovels more pie.

"I thought maybe those of us still Earthbound might want to form a...a—" Cas rubs his face.

"Angel club?"

"Something like that, yes Dean."

"But it was a no go, I'm guessing."

Cas leans back in his chair and sighs. "I don't blame them. They told me after millennia of following heaven's orders, they just wanted to be left in peace. No more rules. No easy way for Heaven to find them if the angels in charge change their mind."

"Hey! Look at the bright side!"

"Which is, Dean?"

"Less angel shit for you. More Netflix with us."

The corners of Cas' mouth twitch up a little at that.

Really, Dean should have left it there, but he was feeling good at having made his friend smile, and it seemed like as good a time as any. In hindsight he should have just said he had a date, but that felt disingenuous because he didn't actually have a date yet nor had he told Sam, so of course he did the worst possible thing. He put the pressure on Cas.

"Hey, Cas...."

"Yes, Dean?"

Dean traces invisible sigils onto the tabletop.

"What is it, Dean?" asks Cas as he scoots closer.

"It's just...now that..." Dean takes a deep breath and fixes his eyes on the pie, "Sam's not dying, and Naomi's not in your head anymore, and I'm not a demon, and Amara's done eating the world...do you think...we could—"

Dean is cut off by the hard slap of Cas' palm in the table. He looks up at Cas in surprise and feels cold at the flat look on his friend's face.

"Damnit, Dean!

"Cas...I—"

Castiel stands up, now glaring at Dean with his smite face. "How many times do we have to go over this, Dean? How many times do I have to tell you 'no'?"

"I just thought that—"

"No, Dean. Stop. No more. You need to stop being delusional about 'us'. I thought you understood how things were."

And yeah, ok. Maybe there was a small part of Dean that had _hoped_ Castiel would tell him they could be together like he wanted, but this whole exercise had been to clear the air so Dean could go on a date with Tyson on a clear conscious. But as much as he's grown as a person, he's still Dean Winchester and he can't just let Castiel stand there and shit on him. So he stands, slamming both his hands down on the table, making the pie fork clatter off the dish and his coffee slosh over the sides.

"You know what? FUCK YOU, Castiel. You stand there and call me delusional, but what is this that we're doing, huh? The staring at me and the nights in my room watching Marvel movies and bringing me my favorite food and texting me weird crap about penguins at 4 in the morning? What about the whole 'profound bond' shit, huh?"

"I thought it was called 'being your friend,' _Dean_ ," hisses Castiel.

"Oh yeah?"

"Yes, Dean."

Dean leans back, crossing his arms.

"And are you friends with Sam?"

Castiel mirrors his pose, eyes smoldering.

"Of course, Dean."

"How many of those do you do with Sam?"

Castiel's mouth opens and closes once, twice.

"I don't see any rabbit food in those bags. No V8. How many times you stay over in Sam's room?"

Castiel's lips purse and Dean can see the effort it takes for him to swallow his anger.

"You are my favorite, Dean. So lawsuit me. But if you recall, you are not the only one of you two whom I raised from perdition."

"I'm the only one you marked," Dean says, punctuating his statement with a finger jab in Castiel's direction.

"An action I eventually rectified," counters Castiel, eyes stormy.

And, ouch. Dean feels like an ice pick was just jammed into his chest. He's pretty sure Castiel only said that to piss him off, but: still. Dean's body slumps, the fight draining from him. He rubs at his eyes with one hand, the other supporting his weight against the chair.

"Yeah. Yeah, ok. Game, set, match."

Seeming to realize he's taken it too far, Castiel's features soften. "Dean, I—"

But Dean cuts him off. "No, no. You're right, Cas. My mistake. I'm, uh, going to go do some research. In my room."

"Dean..."

"Sammy should be home soon. You'll have at least one friend to hang out with tonight."

"Dean, please!"

Dean heads out of the kitchen praying that Castiel won't follow him, and hey—maybe he answers his prayers because Dean doesn't hear any footsteps as he makes his way to his room and locks the door behind him.


	4. Chapter 4

Dean does not do research. He plugs in his headphones and turns on some Zep. He must fall asleep, because at some point later Sam is shaking him awake, face full of concern.

"Hey...wah...Sammy?"

Sam relaxes. "Jesus, Dean. You scared me."

Dean pulls the headphone off and wipes at the drool on the side of his mouth.

"For falling asleep?"

Now that he knows Dean is ok, Sam's bitchface is in full effect. He sits on the chair near Dean's bed.

"No, asshole. You weren't answering your texts, and when I got back there was unfinished pie and spilled coffee in the kitchen. You weren't answering your door either."

Dean eyes the door.

"Pretty sure I locked that."

Sam holds up his lock pick.

"Yeah, you did. What's wrong?"

"Why do think something's wrong?"

It's a game Dean knows he's going to lose, but he figures Sam would be even more concerned if he didn't play it.

"Dean. There's unfinished pie in the kitchen."

"Hey, is Cas around?"

"Is Cas...? No, Dean. Don't change the subject."

Dean blows air out his nose and scrubs down his face again—if he doesn't quit it, he's going to rub it raw.

"Cas and I had a fight, ok? It was stupid, no I don't want to talk about it."

"What did you do this time?"

"What did I...why are you assuming _I_ did anything? Cas can be a dick, too."

Sam lets out a small chuckle. "Ok, I won't pry if you don't want to talk about it. I'm going to trust you that it's not about anything bad."

"Uh, thanks, Sam. I think."

"Of course," Sam says as he claps Dean on the shoulder. "You wanna come finish that pie?" He stands, ready to leave the room.

"Maybe later, Sam. But, uh...there is something—nothing _bad_ , don't give me that look—that I wanted to ask you. Tell you."

"Yeah, Dean. What is it?" says Sam as he sits back down, soulful eyes making an appearance.

Dean picks at his comforter.

"Things are good with Eileen, right?"

"Yeah..."

"And it's nice to have that, right?"

"Yes, Dean...what is this—"

"But what if Eileen wasn't in the life?"

"What do you mean, Dean?"

"If Eileen was still Eileen, but not a hunter. Would you still...?"

Sam takes a moment before responding. "I don't know, Dean. Her being a hunter, having that common ground, being able to talk about the job...it's kinda a big reason I like her."

"Ok, forget Eileen," says Dean as he maneuvers off his bed.

"Dean, what are you trying to say?"

Dean's not afraid to tell Sam he wants to date a dude. He's never come out to Sam, but that's because he hasn't ever felt he had to. So many years in each other's pockets—Dean knows Sam knows. He's not even afraid Sam will torment him for showing his soft underbelly, knows Sam won't jab sharply at it. But he is afraid Sam will veto this for safety reasons. Dean will have to tell Tyson he's not interested, find a new bar, and—oh—the whole blow out with Cas will have been for nothing.

"I want to go on a date."

Sam blinks at him. "Ok...? You go on lots of dates, Dean"

"Like, a _date_ date, Sam. Not an, ah, _casual encounter_."

"Ohhh," Sam says, and Dean can see the light go on. "Hey man, if you and Cas—"

"NOT CAS."

"I...what?"

And there goes Dean's hands over his face again. Really, he's surprised there aren't abrasions.

"The date...the guy. It's not Cas."

Sam's eyebrows shoot up comically into his forehead wrinkles.

"Is that what you and Cas fought about?"

"Jesus Christ, Sammy...no. That's not...why do you keep bringing Cas into this?"

They both stare at each other. Of course Dean knows why Sam is bringing Cas into it, but he doesn't want to have THAT conversation. Not right now. Maybe not ever.

"I just thought..."

Dean can tell it's time he stopped being a 13 year old and rip off the band aid.

"You know Tyson down at the bar? Yes? Yes. Well, he asked me out, said he wanted to see where it could go. And Sam, I'd like to say yes, ok?"

Sam just sits there quietly for a moment.

"Dean, of course it's ok. I'm your brother and I accept you—"

Dean cuts him off by laughing—a full belly laugh—in his face.

"Dude, I'm not coming out to you. I'm asking you if it's ok that Tyson's a civilian."

He expected the indignant bitchface Sam shoots him.

"Dean, you kinda _are_ coming out to me. And excuse me for showing my support."

"Uh, thanks, Sam," says Dean as he puts both hands on each of Sam's shoulders. "But you already know I sleep with guys."

Sam pushes Dean's arms off of him, but he's smiling. He draws Dean into a backslapping hug.

"Fuck you, Dean. I always thought you just didn't know how unsubtle you were being."

Dean musses his hair. "Fuck you too, kid. You pretty much just told me I was a shit hunter."

Sam slaps his hand away. "Don't call me kid, and you kinda are a shit hunter. You've died, way more than I have."

"Hey," Dean jabs at him with his index finger, "I'm only counting that damn Mystery Spot fiasco once."

They laugh—it's an old debate—and Dean follows Sam out of his room.

"But uh, this is really ok with you, man?"

"I'll admit that I'm a little concerned, Dean...but I trust you and you deserve to be happy." Sam stops and looks Dean in the eyes. "You do realize if you guys get serious you'll have to read him in."

Dean sighs. "Lemme just get through the first date, ok Sammy?"

"Ok, Dean."


	5. Chapter 5

Dean sits in the diner booth, tapping his phone on the Formica tabletop. Since he told Tyson he'd be out on a case, he waited 2 days before he called to set up what he'd been referring to as a "pre-date" in his head. Castiel hasn't been back to the bunker nor has Dean received any late-night texts from him.

He's picking at the order of fries set in front of him in the center of the table when he hears the bell and looks up to see Tyson heading his way.

"Hey, man," Dean smiles at him.

Tyson smiles back. "Hi, Dean. Are those up for grabs?" he asks as he takes one.

"I got them for the table."

"Oh, well. I hope the table doesn't mind sharing."

Dean looks at Tyson with horror.

"Ty...that was...that was pretty terrible."

Tyson grabs a handful of fries and shoves them into his mouth as he shrugs.

"Is it a dealbreaker?"

Dean laughs a bit. "It's...naw. No, man. Not a deal breaker. But I can't promise I'll laugh at your jokes just because your cute. You gotta earn it."

Tyson breaks into a wide grin. "All I'm taking from that is that you think I'm cute."

Dean blushes as he gapes like a fish.

The waitress comes over and they order.

"So, Dean," starts Tyson, "what are we doing here? I'll admit when I thought about going on a date with you it didn't involve lunch."

Dean rubs at the back of his neck.

"I know we said we'd see where this went...but there're... _things_ I feel like you should be aware of. Things that have been issues before. And I'd just rather we walk away as friends now than get into this and...well...yeah."

"Well, that's super vague."

"I told you I was a bounty hunter."

"Yeah."

"Well, that means I go on cases all around the country. It's steady work, but it's not consistent. Some of it requires me to be undercover and bend the law. It's dangerous. There are times when I'll just have to pick and and go for a week. There'll be radio silence and I might come back injured. Both my parents died on the job. And I've killed bad guys before. I'll probably kill bad guys again. I won't be able to talk to you about specifics. Oh, also since my brother & I conduct business where we live, my home is off limits."

Tyson stares at him, bug-eyed. Dean can hear the gears grinding in his head. The waitress comes by and drops the food off. Correctly reading the table, she opts to not engage either of them.

"Say something."

Tyson blows his breath out. "Jeez, Dean. Is that...are you serious about all that? You're not just fucking with me?"

Something twists inside Dean and he can't help but wonder if he blew this on purpose. He puts on his best "devil-may-care" look, complete with his nonchalant smirk.

"You can see why I have a reputation for being a one-hit wonder."

"So you've never...?"

"Twice. Cassie left me when she found out what I did for a living. Lisa and I made it a year before...well before she realized I was never gonna give it up."

"No near misses with a guy?"

Dean considers this. Did Castiel count?

"Dean?"

"That's...it's complicated."

"Oh?" Tyson leans forward.

Dean goes to rub his palm over his face, but switches to pinching the bridge of his nose, just for variety.

"There was a guy. He's in the business. It's a long, boring story, but I thought we just needed to get our act together and he apparently was never interested. He, uh...grew up in a religious cult so he's not real good with social cues."

It's really amazing how much Dean is sabotaging this not date. Tyson is gaping at him, and Dean suddenly wants to be anywhere but here. This was such a mistake. He should have just slept with the guy and been a dick about it after. He reaches into his back pocket for his wallet.

"Ok. Yeah," he says. He starts to grab some bills from his fold, but Tyson puts his hand over his.

"So basically you're a bad boy with a heart of gold who just wants to be loved."

Dean doesn't blush. He turns absolutely beet red.

Tyson bursts out laughing. "Fuck, I'm in so much trouble."


	6. Chapter 6

Cas doesn't text again that night, but Dean is too busy to notice. Sam doesn't even ask if the date went well, he just gives Dean a shit-eating grin when Dean tries to sneak into the bunker the next morning.

 

 

 


	7. Chapter 7

Weeks go by and Dean settles into a new routine. Sam and him both do. With Amara taken care of, Crowley managing hell, and the angels quiet for once, the brothers only really go on a couple of milk runs. A salt and burn in South Dakota after which they visit Jody, Alex, & Claire for a family dinner. A vamp nest in Michigan they take out with a couple of other hunters that called them in. Dean bruises a few ribs after he gets slammed into the wall from a poltergeist, and he can't help but laugh—Chuck he missed the simplicity of being manhandled by a disgruntled spirit. Sometimes Eileen joins them and spends the night with Sam. Sometimes the two of them go off on their own hunts, Dean manning the research station.

Dean dates Tyson. He's actually surprised at how easy it is. They eat, they drink, and occasionally the go to the movies—or double with Sam and Eileen playing pool. He and Tyson work through Dean's queue. Tyson is mostly ok with Dean's schedule. As a PhD candidate ("Ooo, fancy. Can I call you doctor?" "Not yet, Dean, but you can call me 'Daddy'." "Never say that again, Ty."), Tyson himself doesn't have a lot of free time—plus he's working part time at the bar to offset his living expenses even though he gets a stipend. They have one big blowup about Dean's time management ("I _told_ you how it would be, Ty" "No, _Dean_ , you told me you'd be gone a lot, not that you'd blow me off when you _were_ here!") and after that he told Sam, "Two nights. I need two nights for myself." On those nights Dean indulges himself as the big spoon and wraps his limbs around Tyson, nose nestled in his hair. After suffering through weeks of rubbery eggs and charred toast, Dean takes over in the kitchen and finally makes Tyson that fritatta. He's not Castiel, doesn't make Dean's insides light up...but Castiel was never easy; Castiel was never any spoon.

Castiel thaws. At first his texts and visits are short, perfunctory. He's all business. He and Dean give each other a wide berth. Sam gives them both his 100% done with this bitchface. One night Dean sees a gif of a llama jumping set to DMX's "Up in Here." It makes him laugh so hard that he sends it to Cas. When he wakes up the next morning, he sees Cas has sent him a gif of a kitten jumping set to Outkast's "Hey Ya." A few days later Cas brings by a DVD of a documentary about bees, and Dean sets up his laptop on the library so Cas, Sam, and he can watch it. He falls asleep, but wakes up to find Cas covering him with a blanket. "Sleep, Dean," he says. So Dean does and when he wakes up it's in his own bed.

Dean doesn't mention Tyson to Cas. Even after everything, Dean still feels cagey about Cas knowing that he's dating. He's careful to say "we" in stead of "me & Ty". He tries to keep movie nights with Cas separate from date nights with Tyson. He says he's going to the bar, but he doesn't add that it's to bother Tyson while he's working.

He knows it's wrong to assume Sam has taken care of the notification, but Dean just pretends that Sam has.


	8. Chapter 8

Dean has been dating Tyson for months and it's...good. It's not apple pie, but Dean gave up apple pie around the time Cas decided that being God was a cool idea. Tyson (mostly) puts up with his shit and in return Dean gives him the TL;DR version of his life which causes Tyson to utter, "Dean, I'm beginning to see a pattern here. Maybe you guys should stop making terrible deals with criminals."

He's not wrong.

 


	9. Chapter 9

 Dean becomes a fixture at Tyson's bar. Occasionally there's some trouble when it becomes obvious that Dean & Tyson are a couple, but it turns out that Bonnie has a mean right hook and a sawed off. It makes Dean miss Ellen that much more.

One night they're playing pool after Tyson's early shift ends and the trouble comes from an unexpected place. Tyson is _shit_ at pool, but Dean likes showing him how it's done, easing himself nice and close behind Tyson, hands sliding up and down Tyson's arms as he maneuvers the cue into position.

" _Dean_...STOP IT," hisses Tyson.

"Whadaya mean? Don'tcha want to learn?," asks Dean coyly as he continues to grind subtly into Tyson's ass.

Tyson's giggle is cut off as the bar door bangs open. Dean is immediately tensed and spring loaded, hand at the gun in his holster, assessing the situation. The situation happens to be a pissed off angel in full smite mode. Cas looks wildly around the bar until his eyes meet Deans. As Cas strides toward them, Dean's hand eases off the gun, but he doesn't relax.

"Dean?" asks Tyson from behind him. At some point Dean had pushed himself in front. Dean doesn't respond because Cas is suddenly there, pure fury in his eyes. Dean shoots a quick look and a shake of the head at Bonnie, whose hand he sees reaching under the bar.

"Cas...?"

"Don't 'Cas' me, Dean? What is this?" Cas makes a sweeping gesture.

"It's a pool table." It's not funny. Dean knows it's not funny.

Cas closes his eyes and Dean can almost hear him counting to 10. When he opens them again he leans forward onto the pool table.

"What. The. Hell. Dean."

He's cursing. Not a good sign.

"You're going to have to give me more than that, Cas."

They both know what this is about. Dean knows what this is about and Cas knows he knows. But it turns out he's actually still kinda pissed that Cas called him delusional, so he's going to be an ass and make Cas work for this.

"You weren't at the bunker."

Ten points from Griffindor for mentioning the secret clubhouse.

"Nope," says Dean, popping the "p."

Cas stares at him, straightening back up.

"Sam said you were here with.... I brought apple pie and _Live Free or Die Hard_."

The fury in his eyes dissipates a little, edged out by...sadness?

"Cas...." Dean's hands are back scrubbing his face. He guesses it's ok, since it's been a while since he abused it in this manner. "It's Friday? Date night? I'm on a date with my..." Dean searches for a term that isn't "boyfriend" and comes up with lover, paramour, and partner. "With my boyfriend."

Cas looks absolutely crestfallen. For about 5 seconds. Then the fury is back and he finally seems to notice Tyson.

"Yes. Sam said," snaps Cas in staccato. "Something which you have failed to mention."

"You haven't really been around much, Cas."

"I've been around enough."

Which is...fair, but Dean's not giving on inch on this. Cas has made him feel like absolute shit for wanting him for so long. He can't turn around now and be incredulous that Dean has moved on. Kinda. The box inside the moat is screaming at him, but Dean can't go back. He just can't go back to lying alone in his bed, the one side still warm from Cas' body. To small touches he savors for too long and declarations made when all seems lost only to be swept under the rug again. He. Can't.

But he's had a lot of practice being just friends with Cas, so he rallies.

"Look, Cas. I'm busy with my guy tonight. Why don't you come back tomorrow and we'll pop in that movie?"

Cas crosses his arms. "Because I'm present now, Dean."

And ok, Cas has been bordering on "petulant child" territory for a while now, and that statement just pushes him clear into it.

"Then I don't know what to tell you. I'm busy now, Cas."

Cas grips the edge of the pool table and Dean hopes no one else notices the sudden hairline fractures that form. There was some initial interest in the altercation when Cas first blew in, but since then people seem to have downgraded it to domestic dispute—which to Dean's displeasure he's noticing it kind of is—and are only glancing over at them occasionally.

"You are doing this to incite my ire. You are doing this to goad me. Because of what I said to you."

Dean has done a really good job of not being himself throughout this whole exchange. He doesn't know if Cas actually thinks that or if he's trying to piss Dean off, but it breaks his resolve. The whole point of that disastrous conversation was to give Cas the head's up on Tyson and now Cas is implying the Dean has being dating Tyson for months just for the moment it would make Cas jealous.

Because Cas _is_ jealous.

"You know what, Cas? You come storming in here making a scene when you know how much I hate—"

"Oh please, Dean. You are the most dramatic creature I have ever had the pleasure of meeting and that includes Balthazar."

"Yeah, how is old Balthy, Cas?"

It's a low blow and Dean hates himself the second the words leave his mouth. Cas' face crumples and he seems to cave in on himself. It twists at Dean's guts, but for some reason his mouth hasn't caught on to the fact that it's time to shut the fuck up and do damage control.

"Maybe it's not that your brothers in arms don't want to unionize. Maybe they just don't want to unionize with you."

Dean really can't believe he just said that, doesn't even know where the thought came from. He certainly doesn't even believe the statement. But Cas does. Oh boy, does he. It's like all the strings holding him up have just been cut.

"Shit, Cas. I'm sorry. I didn't mean—"

"No, no. You're right, Dean." He looks dazedly around the bar. "I see I am unwelcome here. I'll just...I'll just go, then."

Dean makes to go after Cas, but he feels the weight of Tyson's hand on his arm. He knows if he goes after Cas, it's over with Tyson—which isn't fair because Dean & Sam are all Cas has and Dean shouldn't be the one shitting on Cas. He wavers and he know his hesitancy is costing him trust points with Tyson, but Tyson is just some guy Dean met a few months ago and Cas is...Castiel, Angel of Thurday: guy who saved Dean from hell and fell for him and died for him. When he thinks of it that way, he can see there's no contest.

But he doesn't go after Cas.


	10. Chapter 10

Dean texts Sam: _Cas showed up at bar. some shit went down. we were both assholes but I went to far. look after Cas. I hafta clam Ty down._

He turns off his phone.


	11. Chapter 11

 After Cas left, the mood had soured. Dean and Tyson silently closed their tab, collected their belongings, and headed back to Tyson's studio. It wasn't until they were both lying in Tyson's bed, next to each other but not touching, that Tyson spoke.

"Dean. What the fuck was that?"

Dean sighs. "I want to answer you, but I don't even know where to begin."

"I'm going to ignore all the weird shit I heard that must be a part of your job. I'm just going to focus on that dude who seemed jealous as fuck. I thought all your exes were women."

Dean shifts in the bed so that he's on his side, facing Tyson. He runs his hand up and down Tyson's arm, bolstered when Tyson doesn't flinch away.

"You know that guy I did tell you about?"

"Cult guy?"

"Is that how you think of him? 'Cult guy'?"

"Maybe."

Dean huffs a small laugh.

"Yeah, well, That was him."

Tyson is silent for a while.

"That's the guy who you're sure has no romantic interest in you."

Dean stops stroking Tyson's arm and sits up.

"I've known Cas for over a decade. I've asked him out several times, actually. Not just once. Last time I asked him if he was sure, he yelled at me and called me delusional. It's why he hasn't been around. We haven't been on good terms."

Tyson is quiet again.

"What did he mean when he said you were seeing me just to goad him?"

"So the thing is, Cas and I have been through a whole hell of a lot together. Some life and death shit. Bad shit. You already know that after dad died Sam & I made a lot of...terrible decisions. Bad deals. Cas' family was actually part of those. He, uh, kinda left his cult for us. Helped us navigate out to the other end at the cost of his home and his family. Sam & I basically adopted him, taught him the family business. But it hasn't always been smooth sailing. He tried to fix some shit and it went sideways in a big way. He let some power go to his head and it came between us for a time. But he paid for it, and family's family, so Sam & I took him back. He's never really recovered. I shouldn't've said that crap to him. It was out of line."

"Oookay..." starts Tyson. "That was super vague, Dean. I can't say I followed your entire thread, but what does that have to do with us?"

"I guess I needed you to understand that Cas isn't just some business associate or friendly acquaintance. He gave up his whole world for us. He's saved our lives, literally. He does his own thing most of the time, but he's part of Sam and my operation. He has his own room when he needs it."

"Dean—"

"So when you kissed me and said you'd be willing to see where this went, I felt like I owed Cas a chance to tell me not to."

Tyson sits up. "You did _what_?!"

"Calm your tits! I didn't think he was magically going to change his mind. I just..." Dean huffs a laugh, "I just wanted to avoid a scene where Cas came crashing into a bar demanding what gave me the right to have a boyfriend. I _told_ you: religious cult; social cues. I had every intention of telling him about you, but things got heated, words were said, and it...devolved. There's a possibility I might have stormed off. There may have been huffing."

They're both silent until Tyson says, "I'm still hurt, but I can kinda see your logic."

"Are we good then?"

"We're good, Dean. But Cas can't just come storming into the bar. And if you want to work out with me, you're going to have to work out the bullshit with him."

"Yeah, yeah. Let's go to sleep."

They do not have sex that night.


	12. Chapter 12

Dean goes back to the bunker early instead of making Tyson pancakes. It's his compromise for not going after Cas at the bar. He left a note reading: _working out the bullshit. IOU magic fingers ;)_

Last time he tried sneaking back into the bunker at the crack of dawn, Sam was waiting for him with that shit-eating grin and a cup of coffee. This time he's met with Sam's bitchface and a cup of extra bitchface.

"What the hell, Dean?!"

"I know, Sam. Is, uh...Cas around." Dean swings around Sam and takes a seat in the war room. Sam follows him.

"No, Dean. Cas isn't around. What the fuck did you say to him? He was beside himself, saying all sorts of shit about bad deeds and atonement."

"Fuuuuuuck," says Dean, giving up and and rubbing his raw. Sam is just standing over him, arms crossed, foot tapping in frustration. "Look, Sammy—I know I fucked up. Cas pissed me off and I lashed out."

"Cas pissed _you_ off."

"Yes. Sam. Cas pissed _me_ off."

"And how. Dean. Did he piss you off?"

Dean slams his palms on the table.

"He came storming into the bar like he was going start smiting left and right. You know we're supposed to keep a low profile in our own backyard. Then he starts demanding that I just _leave_ because he deigned to visit us."

"You used to like it when Cas stayed, Dean."

"I _do_ like it when Cas stays, Sam. But I was busy, wasn't I? Cas wanted me to leave mid-date just because he said so. Then he insults Tyson by outright saying I'm only dating the guy to piss him off."

"He said that?"

"To. Our. Faces. I know it's Cas, man—but he can't insult my...boyfriend."

"He didn't tell me that."

Dean snorts. "I bet he didn't. And then he called me: _dramatic_."

It's Sam's turn to snort. "Well, you are a bit—"

"Shut your face, Sam."

Sam holds up his hands in mock surrender.

"That's when I said the wrong shit."

"Which was...?"

"Look, it was hurtful. I'll admit that. I don't feel like revisiting it with you. I'll apologize to Cas for being a dick, but he was out of control."

Sam pulls a chair around and sits next to Dean.

"C'mon, man. You know why. Can you blame him."

"Yes, Sam. I _do_ know why. Do you?"

The puppy dog eyes come out. Dean's not getting out of the feelings talk.

"I've been wanting to talk to you about this for a while, Dean."

He pauses and Dean makes a "go on" roll with his hand.

"Look, I'm happy for you—I really am. I meant it when I said I just wanted you to be happy."

"But..."

"But I don't understand why you're not dating Cas. I guess I always thought you were holding back because of some gay panic shit. But now you're happily dating a dude and it's not Cas."

"Cas is an angel, his vessel is a—"

" _I know_ , Dean, but the parts are—"

"Jesus, Sammy, can we roll credits here?"

"I don't understand why you're hurting him. If it's not the guy thing, what is it? Is it because he's an angel? You have to know Cas doesn't care. He just wants you. He's so distraught that you're—"

"SAM. Stop. Just...stop." Dean is beginning feel itchy.

"No Dean—"

"Sam, Cas doesn't want me. Let it go." Dean can feel his heart starting to pound faster.

"Of course Cas wants you, Dean."

"No, Sam. He really doesn't. Can you just drop it?" There's a tightness in Dean's chest that's making it really hard for Dean to remain calm.

"No! If this is some self-worth issue that stopping you from—"

Dean stands up abruptly, grabs a lamp and throws it across the room. It's plugged in, so it doesn't go very far before it's bungied back, but it still shatters on impact.

"WHAT THE FUCK, DEAN."

Dean is panting heavily now, and it's possible he's crying, or it might just be sweat.

"YOU DON'T KNOW, SAM. You sit here telling me that all I need to do to have Cas is to get over myself. That you feel bad for Cas because I won't reciprocate his _profound_ love for me. BUT GUESS WHAT. I've been telling Cas I love him for years. I've been begging Cas to be with me for years. _Years_ , Sammy. And he rejects me. Every. Single. Time. And I thought I was ok with it, but then I met Tyson and Tyson actually wanted all of me, Sam. And still, _still_ , I held out hope that maybe this time _this time_ , Cas might want me. And you know what he said to me? Huh, Sam? Do you know? _Do you_?"

"I...I...uh..."

"Guess, Sammy. Go 'head."

"That...that he wasn't ready...?"

Dean lets out a guffaw, knowing full well he's into the danger zone and wondering if there's still a bottle of Jim in his room.

"That I was 'delusional' to think he could ever want me. That our profound bond was a mistake he tried to rectify."

The color drains from Sam's face and he can do nothing but open and close his jaw. Dean's sure he's definitely leaking tears by now.

"So yeah, maybe I said some shitty things to Cas, but you can't just...you can't just say that shit to people—and Cas has been down here long enough to know that—and then get mad when they move on."

Sam still doesn't say anything.

"So if you and the entire fucking world could get the fuck off my back about Cas, I'd really fucking appreciate it. I'm going to my room. Don't fucking pick my lock again."

Dean storms off to his room knocking anything and everything in his way over. So he's dramatic. So fucking what.


	13. Chapter 13

Sam sits there and thinks about everything that Dean has just said. He goes for his early run and thinks about everything that Dean has said. He makes his avocado smoothie still thinking over what Dean said. He stands in the shower, thinking.

Dean doesn't leave his room the entire day.

Sam texts him: _You alive? Just checking._

Dean: _alive. fuck off_

Sam lies in bed. Thinking.


	14. Chapter 14

Dean appears the next morning, duffle bag in hand.

Sam squints at it. Christ he's been spending too much time around Cas.

"It's not a Ty night, is it?"

Dean grabs a cup of coffee, but doesn't sit down.

"No, it's not. I need to blow off some steam. I'm gonna go salt and burn some bones. Maybe get slammed against a wall."

"Dean..."

Dean holds his hand up.

"I'm not mad at you, Sam. I just need some space and something to hit. I call you after it's done and head back after I get some shut eye. Two days, max."

He leaves and Sam doesn't stop him.

**Notes for the Chapter:**

> More to come, stick with me!


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